Cheswick is a small town located on the north bank of the Allegheny river about fourteen miles above its junction with the Monongahela river where they form the Ohio River. Cheswick Borough was organized about 1901. Harry E. Armstrong was instrumental in getting a charter for the Borough and served as Cheswick’s first burgess. The Borough was incorporated on March 4, 1902. Cheswick was divided geographically into two parts; the flat, wide, level part extending from the river to the foot of the hill. On the slope of the hill was situated the second part of the future mile square borough. Freeport Road (known as Freeport Road or Pittsburgh Street depending upon the geographical area) was unpaved and ran thru the center of town and formed part of the highway from Pittsburgh to Freeport. Along the sides of the road were boardwalks and cinder paths for pedestrians.

John Pillow was one of the first to build within the borough limits. He owned most of the land within the present borough limits and divided it among his three sons (George, Thomas and Archibald). The remainder was owned by an Englishman, Henry Kellett. There were three smaller plot owners between the canal and the river. The canal which went from Pittsburgh to Philadelphia was abandoned in the early 1860’s and the West Penn branch of the Pennsylvania Railroad was in operation in 1866. In 1875 there were fourteen houses within the borough limits. Seven of the houses were located between the railroad and the river. Eventually there were possibly seven cottages to the east of the houses right by the river. Since there were no dams in the river at the time and it would almost dry up in the summer, there was much more space for construction close to the river. Between Freeport Road and the railroad were the houses of Robert Stewart, Archie Pillow and Matthew Maclean. North of Freeport Road were the houses of George and Thomas Pillow. In 1836 Matthew Maclean bought Henry Kellett’s property, 29 acres, and added to the one room dwelling that was on the property. Eventually this house had two more additions to it with the new front of the building facing the railroad and river. Some railroad men purchased fifty acres from Mrs. George Pillow and laid it out in lots with Highland Avenue being the main street. They were only able to sell a few lots and eventually sold the remainder of the plot to Harry E. Armstrong. He erected several houses hoping to start a building boom. However, he also met with disappointment and lost everything he had invested. His efforts in organizing the Borough was the means of getting people interested and a steady growth began which has continued to the present. Over the years numerous businesses have made Cheswick their home. Businesses like theaters, hardwares, food establishments, medical facilities, manufacturing, auto service stations and repair, lumber yard, shoe and clothes stores , etc. have done well over the years along Pittsburgh Street.

Today the Borough is referred to as a "Community of Homes."

The 2010 census population of Cheswick was 1,746.